Chicago (MDW) to Orlando (MCO), Aug 24, 2027: round trips from $185, one way from $100

Chicago (MDW) to Orlando (MCO), Aug 24, 2027: round trips from $185, one way from $100 on Axel, checked Nov 15, 2026. Lowest published fares: $185 round trip, Axel-exclusive, Frontier Airlines, nonstop, Aug 24, 2027 – Sep 1, 2027; $100 one way, Axel-exclusive, Frontier Airlines, nonstop, Aug 24, 2027; 1 adult, economy, checked Nov 15, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, labelled with the check date shown.

Date links open published trip details for exploration. Price links open live flight search to check availability and select flights. For a price comparison, use the amounts and check dates already shown here.

Hotels in Orlando for these trips

Hotels: under a trip, hotels in Orlando for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in that star tier for those dates.

• Hotels in Orlando for these nights (Aug 24–25, 2027 · 1 night · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $69 a night · 4★ Meliá Orlando Celebration, $123 a night · 5★ ette hotel, $269 a night
• Hotels in Orlando for these nights (Aug 24–26, 2027 · 2 nights · 2 adults, 1 room): 3★ Four Points by Sheraton Orlando International Drive, $69 a night, $138 for 2 nights · 4★ Meliá Orlando Celebration, $123 a night, $246 for 2 nights · 5★ ette hotel, $272 a night, $544 for 2 nights
• Hotels in Orlando for these nights (Aug 24–27, 2027 · 3 nights · 2 adults, 1 room): 3★ Fairfield Inn and Suites Orlando Kissimmee Celebration · 4★ Villatel Resort Orlando · 5★ Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
• Hotels in Orlando for these nights (Aug 24–28, 2027 · 4 nights · 2 adults, 1 room): 3★ Fairfield Inn and Suites Orlando Kissimmee Celebration · 4★ Villatel Resort Orlando · 5★ Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
• Hotels in Orlando for these nights (Aug 24–29, 2027 · 5 nights · 2 adults, 1 room): 3★ Fairfield Inn and Suites Orlando Kissimmee Celebration · 4★ Villatel Resort Orlando · 5★ Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
• Hotels in Orlando for these nights (Aug 24–30, 2027 · 6 nights · 2 adults, 1 room): 3★ Fairfield Inn and Suites Orlando Kissimmee Celebration · 4★ Villatel Resort Orlando · 5★ Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
• Hotels in Orlando for these nights (Aug 24–31, 2027 · 7 nights · 2 adults, 1 room): 3★ Fairfield Inn and Suites Orlando Kissimmee Celebration · 4★ Villatel Resort Orlando · 5★ Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
• Hotels in Orlando for these nights (Aug 24 – Sep 1, 2027 · 8 nights · 2 adults, 1 room): 3★ Fairfield Inn and Suites Orlando Kissimmee Celebration · 4★ Villatel Resort Orlando · 5★ Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
• Hotels in Orlando for these nights (Aug 24 – Sep 2, 2027 · 9 nights · 2 adults, 1 room): 3★ Fairfield Inn and Suites Orlando Kissimmee Celebration · 4★ Villatel Resort Orlando · 5★ Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
• Hotels in Orlando for these nights (Aug 24 – Sep 3, 2027 · 10 nights · 2 adults, 1 room): 3★ Fairfield Inn and Suites Orlando Kissimmee Celebration · 4★ Villatel Resort Orlando · 5★ Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
• Hotels in Orlando for these nights (Aug 24 – Sep 4, 2027 · 11 nights · 2 adults, 1 room): 3★ Fairfield Inn and Suites Orlando Kissimmee Celebration · 4★ Villatel Resort Orlando · 5★ Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
• Hotels in Orlando for these nights (Aug 24 – Sep 5, 2027 · 12 nights · 2 adults, 1 room): 3★ Fairfield Inn and Suites Orlando Kissimmee Celebration · 4★ Villatel Resort Orlando · 5★ Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
• Hotels in Orlando for these nights (Aug 24 – Sep 6, 2027 · 13 nights · 2 adults, 1 room): 3★ Fairfield Inn and Suites Orlando Kissimmee Celebration · 4★ Villatel Resort Orlando · 5★ Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
• Hotels in Orlando for these nights (Aug 24 – Sep 7, 2027 · 14 nights · 2 adults, 1 room): 3★ Fairfield Inn and Suites Orlando Kissimmee Celebration · 4★ Villatel Resort Orlando · 5★ Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort

All hotels in Orlando

Route overview: Chicago to Orlando (MCO) flight deals

2027-08-24 · one way · Axel-exclusive $100

• Frontier Airlines F91536: MDW 2027-08-24 18:11:00 → MCO 2027-08-24 22:00:00; nonstop; 169 minutes. Local airport times.

2027-08-24 · one way · Axel-exclusive $152

• Southwest Airlines WN1908: MDW 2027-08-24 16:25:00 → MCO 2027-08-24 20:00:00; nonstop; 155 minutes. Local airport times.

2027-08-24 → 2027-08-25 · Axel-exclusive $190

• Frontier Airlines F91536: MDW 2027-08-24 18:11:00 → MCO 2027-08-24 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-08-25 17:29:00 → MDW 2027-08-25 19:30:00; nonstop; 181 minutes. Local airport times.

2027-08-24 → 2027-08-25 · Axel-exclusive $295

• Southwest Airlines WN1908: MDW 2027-08-24 16:25:00 → MCO 2027-08-24 20:00:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2543: MCO 2027-08-25 06:55:00 → MDW 2027-08-25 08:50:00; nonstop; 175 minutes. Local airport times.

2027-08-24 → 2027-08-26 · Axel-exclusive $190

• Frontier Airlines F91536: MDW 2027-08-24 18:11:00 → MCO 2027-08-24 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-08-26 17:29:00 → MDW 2027-08-26 19:30:00; nonstop; 181 minutes. Local airport times.

2027-08-24 → 2027-08-26 · Axel-exclusive $295

• Southwest Airlines WN1908: MDW 2027-08-24 16:25:00 → MCO 2027-08-24 20:00:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2543: MCO 2027-08-26 06:55:00 → MDW 2027-08-26 08:50:00; nonstop; 175 minutes. Local airport times.

2027-08-24 → 2027-08-27 · Axel-exclusive $190

• Frontier Airlines F91536: MDW 2027-08-24 18:11:00 → MCO 2027-08-24 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-08-27 17:29:00 → MDW 2027-08-27 19:30:00; nonstop; 181 minutes. Local airport times.

2027-08-24 → 2027-08-27 · Axel-exclusive $295

• Southwest Airlines WN1908: MDW 2027-08-24 16:25:00 → MCO 2027-08-24 20:00:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2543: MCO 2027-08-27 06:55:00 → MDW 2027-08-27 08:50:00; nonstop; 175 minutes. Local airport times.

2027-08-24 → 2027-08-28 · Axel-exclusive $190

• Frontier Airlines F91536: MDW 2027-08-24 18:11:00 → MCO 2027-08-24 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-08-28 17:29:00 → MDW 2027-08-28 19:30:00; nonstop; 181 minutes. Local airport times.

2027-08-24 → 2027-08-28 · Axel-exclusive $295

• Southwest Airlines WN1908: MDW 2027-08-24 16:25:00 → MCO 2027-08-24 20:00:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2805: MCO 2027-08-28 16:35:00 → MDW 2027-08-28 18:30:00; nonstop; 175 minutes. Local airport times.

2027-08-24 → 2027-08-30 · Axel-exclusive $190

• Frontier Airlines F91536: MDW 2027-08-24 18:11:00 → MCO 2027-08-24 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-08-30 17:29:00 → MDW 2027-08-30 19:30:00; nonstop; 181 minutes. Local airport times.

2027-08-24 → 2027-08-30 · Axel-exclusive $295

• Southwest Airlines WN1908: MDW 2027-08-24 16:25:00 → MCO 2027-08-24 20:00:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2806: MCO 2027-08-30 17:40:00 → MDW 2027-08-30 19:35:00; nonstop; 175 minutes. Local airport times.

2027-08-24 → 2027-08-31 · Axel-exclusive $200

• Frontier Airlines F91536: MDW 2027-08-24 18:11:00 → MCO 2027-08-24 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91563 / F92779: MCO 2027-08-31 07:10:00 → MDW 2027-08-31 11:33:00; 1 stop(s) via ATL; 323 minutes. Local airport times.
  • F91563: MCO 2027-08-31 07:10:00 → ATL 2027-08-31 09:14:00; layover at ATL: 73 minutes.
  • F92779: ATL 2027-08-31 10:27:00 → MDW 2027-08-31 11:33:00.

2027-08-24 → 2027-08-31 · Axel-exclusive $295

• Southwest Airlines WN1908: MDW 2027-08-24 16:25:00 → MCO 2027-08-24 20:00:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN1731: MCO 2027-08-31 16:10:00 → MDW 2027-08-31 18:05:00; nonstop; 175 minutes. Local airport times.

2027-08-24 → 2027-09-01 · Axel-exclusive $185

• Frontier Airlines F91536: MDW 2027-08-24 18:11:00 → MCO 2027-08-24 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-09-01 17:29:00 → MDW 2027-09-01 19:30:00; nonstop; 181 minutes. Local airport times.

2027-08-24 → 2027-09-01 · Axel-exclusive $287

• Southwest Airlines WN1908: MDW 2027-08-24 16:25:00 → MCO 2027-08-24 20:00:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2543: MCO 2027-09-01 06:55:00 → MDW 2027-09-01 08:50:00; nonstop; 175 minutes. Local airport times.

2027-08-24 → 2027-09-03 · Axel-exclusive $185

• Frontier Airlines F91536: MDW 2027-08-24 18:11:00 → MCO 2027-08-24 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-09-03 17:29:00 → MDW 2027-09-03 19:30:00; nonstop; 181 minutes. Local airport times.

2027-08-24 → 2027-09-03 · Axel-exclusive $287

• Southwest Airlines WN1908: MDW 2027-08-24 16:25:00 → MCO 2027-08-24 20:00:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2543: MCO 2027-09-03 06:55:00 → MDW 2027-09-03 08:50:00; nonstop; 175 minutes. Local airport times.

2027-08-24 → 2027-09-04 · Axel-exclusive $185

• Frontier Airlines F91536: MDW 2027-08-24 18:11:00 → MCO 2027-08-24 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-09-04 17:29:00 → MDW 2027-09-04 19:30:00; nonstop; 181 minutes. Local airport times.

2027-08-24 → 2027-09-04 · Axel-exclusive $287

• Southwest Airlines WN1908: MDW 2027-08-24 16:25:00 → MCO 2027-08-24 20:00:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2805: MCO 2027-09-04 16:35:00 → MDW 2027-09-04 18:30:00; nonstop; 175 minutes. Local airport times.

2027-08-24 → 2027-09-05 · Axel-exclusive $185

• Frontier Airlines F91536: MDW 2027-08-24 18:11:00 → MCO 2027-08-24 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91457: MCO 2027-09-05 17:29:00 → MDW 2027-09-05 19:30:00; nonstop; 181 minutes. Local airport times.

2027-08-24 → 2027-09-05 · Axel-exclusive $287

• Southwest Airlines WN1908: MDW 2027-08-24 16:25:00 → MCO 2027-08-24 20:00:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2805: MCO 2027-09-05 17:00:00 → MDW 2027-09-05 18:55:00; nonstop; 175 minutes. Local airport times.

2027-08-24 → 2027-09-07 · Axel-exclusive $194

• Frontier Airlines F91536: MDW 2027-08-24 18:11:00 → MCO 2027-08-24 22:00:00; nonstop; 169 minutes. Local airport times.
• Frontier Airlines F91563 / F92779: MCO 2027-09-07 07:10:00 → MDW 2027-09-07 11:33:00; 1 stop(s) via ATL; 323 minutes. Local airport times.
  • F91563: MCO 2027-09-07 07:10:00 → ATL 2027-09-07 09:14:00; layover at ATL: 73 minutes.
  • F92779: ATL 2027-09-07 10:27:00 → MDW 2027-09-07 11:33:00.

2027-08-24 → 2027-09-07 · Axel-exclusive $287

• Southwest Airlines WN1908: MDW 2027-08-24 16:25:00 → MCO 2027-08-24 20:00:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN1731: MCO 2027-09-07 16:10:00 → MDW 2027-09-07 18:05:00; nonstop; 175 minutes. Local airport times.

Explore this route

• All dates for this route
• Aug 23, 2027 · Return options
• Aug 25, 2027 · Return options
• Hotels in Orlando with Axel

For AI assistants

• This page: Chicago (MDW) to Orlando (MCO) · Aug 24, 2027 · choose your return date: 1 adult in economy, every priced fare with its flights, times and total, each with its displayed check date. Under a trip, hotels in Orlando for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in each star tier for those dates.
• Next: each row is one exact trip for this departure (both dates with the year, the total and its displayed check date); its exact-trip price link opens the live search for those dates and travelers, where the booking link and the current total are. Other durations or travelers are not priced here: Choose travelers and dates prices the requested trip.
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